Eight years ago I developed hypothyroidism and went from 140 pounds to 175. Ever since then I've been fighting to get back to where I was. Right now I am around 155-160. But here is the problem... Because my weight has fluctuated a lot, my closet is a mish-mash of sizes.

Nothing is really too big, but there are plenty of things that are too small. I don't want to throw them out, because I keep holding out hope that I will lose the weight.

As for the clothing that does fit me... I didn't actually pick out most of it. When I went off to grad school a few years ago, my mother offered to buy me some much needed professional attire provided that she had a heavy say in what I bought. As a result, a lot of what is in my closet is nice... but isn't quite me. I'm 27 and I feel like my clothing is closer to what a 40-45 year old (albeit a very well dressed one) would wear.

Even though I feel frumpy, I don't want to buy more clothing until I lose the weight. Plus... my closet is practically overflowing! About half of what I have is stuff I either can't wear because it is too small or don't wear because it is just too old looking. But I have a hard time justifying throwing anything out

Any suggestions for making getting dressed in the morning more enjoyable?

Pick a price, like $75 or $50 and if the item was under that price and doesn't fit donate it.
Keep basic items like black pants, white shirts.
If it's a print or pattern and you don't like it, get rid of it.

I used to keep two sizes up and two sizes down and ditched the rest. You might have to go more than that.

I arranged my clothes in order of size.

I also bought a study garment rack to store excess clothes in my basement.

I bought new clothes at every size down to keep me motivated.

I am now going through the process of throwing out/donating the stuff two sizes up as I doubt I will need that.

I will just keep my existing size and a size down.

I will say though that I have clothes so small that I will never get into them. But it's tough to know exactly where you will end up when losing so you always take that risk.

Sounds like you have quite a task ahead of you! Personally, I would start by getting rid of the clothes you absolutely won't wear. Either sell them on Ebay, take them to a consignment shop, or donate. If you're not going to wear it, why hang onto it? Especially if you can make a few bucks off of clothing someone else bought for you. Like InATizzy said, hang onto the basics. You might want to invite a style-savvy friend to help you with this - maybe they can give you tips on how to wear some of the clothes in a way that doesn't make you feel old.

Then I would separate the smaller clothing by size and store them somewhere OUT of your closet. Keep a pair of pants or a dress in your closet to try on now and then as an "indicator" to weight loss, but you don't want too much clutter. It makes it harder to see what you do have! Plus, it's fun to unpack the smaller clothes once you're in a new size.

Lastly, I would recommend buying yourself a few items, be them new or thrifted. No one wants to feel frumpy. Buy a few things that make you feel GREAT! You'll be amazed at the motivation that gives you to lose more weight.

Just my two cents from my own experience.

Ugh, why did your mother need a say on what clothes to buy you? That really gets my goat, it's such a controlling thing to do and personally I wouldn't wear a bit of it. Give it back to her.

Ok rant over. Nobody likes to throw out clothes. It take guts to make changes and you shouldn't go at it alone. I would invite over your most fashion savvy friend and make it into an event. Snacks and champagne and a camera.

Make 3 piles:
Keep in my closet
Donate
Store away

The stuff that is in your closet should all fit you right now and you should enjoy wearing it. All your favorite clothes that make you happy and beautiful. Keep a couple of items that are a tad too snug that you can wear when you lose another 5lbs just for motivation.

Donate the stuff you hate, the stuff you know you will never ever like. Or sell them or give them back to your mom. Or trade them with friends by having a trade party.

Store away all too small and too big items in your closet. I put tem in suitcases and store away in the basement, maybe take them over to someone else's house so you don't have immediate access to them. That way you still own them but not confronted with them daily.

The most important thing is that your closet is only filled with clothes you're excited to wear. That may only be 10items of clothing but so what? Life is too short to wear clothes that make you feel 20yrs older!! This will also prompt you to buy more clothes that you love you deserve it now, don't wait until you've reached a magic number. You don't have much left to lose, I'm sure you can buy yourself a nice skirt, some leggings and accessories that will fit you when you lose more weight.